N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide → N-Hydroxy-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 570974

反応式

HRID 570974 の反応式
C([O:8][NH:9][C:10]([C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH3:22])[N:18]=[N:17][C:16]=12)=[O:11])C1C=CC=CC=1>C(OCC)(=O)C.CN(C=O)C.[Pd]>[OH:8][NH:9][C:10]([C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH3:22])[N:18]=[N:17][C:16]=12)=[O:11]

参加物

4

反応物 1

HCID 49869276N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

生成物 1

HCID 135985859N-Hydroxy-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide収率 25%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 22989253N,N-dimethylformamide ethyl acetate溶媒

実験手順

A solution of N-(benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (200 mg, 0.67 mmol) and 10% Pd/C (20 mg) in ethyl acetate:DMF (5:1) (36 mL) was put under an atmosphere of hydrogen for 3 days. The mixture was filtered through a pad of Celite™ and the filtrate was concentrated under vacuum. The residue was suspended in ethyl acetate and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether to give the pure title compound as a pale orange solid (35 mg, 25% yield). δH (DMSO-d6): 11.2 (1H, s), 9.18 (1H, s), 8.82 (1H, s), 3.86 (3H, s).

後処理

  1. filtrationThe mixture was filtered through a pad of Celite™
  2. concentrationthe filtrate was concentrated under vacuum
  3. filtrationthe precipitate was filtered
  4. washwashed successively with water, ethyl acetate and diethyl ether

出典と根拠

ORDレコード
ord-3d74d080c0404d81b0bf1e51b7056b7c
出典データセット
uspto-grants-2015_05
特許番号
US09024018B2

関連ノート

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